Matt Damon
Edward Bell Wilson
Angelina Jolie
Margaret Ann Russell
Billy Crudup
Arch Cummings
Robert De Niro
Bill Sullivan
Keir Dullea
Senator John Russell, Sr.
Michael Gambon
Dr. Fredericks
Martina Gedeck
Hanna Schiller
Timothy Hutton
Thomas Wilson
Mark Ivanir
Valentin Mironov #2
Gabriel Macht
John Russell, Jr.
Eddie Redmayne
Edward Wilson Jr.
John Sessions
Valentin Mironov #1/Yuri Modin
John Turturro
Raymond Brocco
Yelena Shmulenson
Dollar Woman
Jack Martin
Dollar Little Boy
Anne-Marie Cusson
Philip Allen's Secretary
Robert Bermudez Cordell
Bay of Pigs Voiceover (voice)
David Crommett
Spanish Translator
Michael Arden
Pinafore Actor
Justin Bohon
Pinafore Actor
Justin Daniel
Pinafore Actor
Michael Flanigan
Pinafore Actor
Will Reynolds
Pinafore Actor
Michael Seelbach
Pinafore Actor
Ryan Michael Shaw
Pinafore Actor
Stephen Powell
HMS Pinafore Singer
Henry Gummer
Bonesman / Boatswain
Gregory Marcel
Dancing Skeleton
Austin Williams
Young Edward Wilson
Sophie Sutton
Connie Wilson
Tessa Kim
Mr. Haupt's Translator
Rob Barnes
Man at Jazz Club
Lee Bryant
Mrs. John Russell, Sr.
Redman Maxfield
Older Bonesman 1940
John C. Whitehead
Reverend Collins
Jeff Skowron
Deer Island Crooner 1940
Oleg Shtefanko
Ulysses / Stas Siyanko
Meredith Deacon
John Russell, Jr.'s Girlfriend
Josh Casaubon
Army Man 1940
Christopher Evan Welch
Photography Technical Officer
Tuc Watkins
Sound Technical Officer
Eric Lindh
Tailor Shop Guard
Trace Taylor
Cryptographer
Amanda Barron
Cryptographer
James Faulkner
Lord Cooper
Robert Ian Mackenzie
Cambridge Club Butler
Sándor Técsy
Sasha, Ulysses' Aide
Tommy Nelson
Edward Wilson Jr. - Age 6-7
Greg Plitt
Guard with Sullivan
Jeff Applegate
Michael Johnson
Sandee Conrad
Edward's Secretary
Jonathan Dokuchitz
Husband Dinner Guest
Susan Haskell
Wife Dinner Guest
Neal Huff
Teletype Operations Officer
Jason Butler Harner
Teletype Communications Officer
Amy Wright
Safe House Operations Officer
Matthew Humphreys
Cherry Orchard Actor
Karron Graves
Cherry Orchard Actress
Robert C. Kirk
Laura's Taxi Driver
Reathel Bean
'Dame' Bonesman
Jerry Coyle
'Dame' Bonesman
Wally Dunn
'Dame' Bonesman
Roger Rathburn
'Dame' Bonesman
Michael Melvoin
Piano Player
Glenn Kalison
Telephone Operations Officer
John Knox
Technical Service Officer
Benjamin Eakeley
Bonesman 1960
Gino Cafarelli
Palmi's Bodyguard
Tommy DeVito
Palmi's Bodyguard
Isabella Cimato
Palmi's Granddaughter
Jimmy Marchese
Palmi's Grandson
Robert Prescott
Bonesman MC 1961
Bill McHugh
Reverend Christiansen
Ann Hampton Callaway
1961 Deer Island Singer
Christopher Druckman
FBI Agent
John Henry
Philip Allen's Driver
Dave Payton
College Student (uncredited)
Vladislav Kozlov
Executioner (uncredited)